My brother and I have a little real estate and are thinking of picking up some more. Also, we do a little light stock trading. We each try to contribute $1K per month into our side projects. It helps alot to have somebody to work with who shares the same investment philosophy, has the same financial background, and the same goals. I'd be careful dealing with family though unless you agree on all of the things I mentioned above.

Just getting started in it. The toughest part is making sure you cashflow. Taxes, insurance, and vacancies can be a killer. Make sure to look up property taxes for that specific property and get the # right before you buy. Next, factor in insurance and leave a cushion for premium increases. Finally, factor in a couple months of vacancy per year (could be up or down depending on market). We grew up in the neighborhood we are buying in so we are very comfortable knowing whether a property is a good deal or not. I wouldn't buy in an area unless I was very, very confident the property will gain big value in the long haul. Our goal is to break even at the least and be able to see it for a good chunk more than what we got it at. If rent go up significantly over time in the area, we will cashflow earlier than expected.

Hassle depends on the quality of the property and the quality of your tenants, which is tough to quantify. Also, I am not a real expert so I would try to get advice from someone who isn't as green as me....

you can look at Dividend stocks. With research you can find 10% payers or bettter, but they will be risky. I would need to buffer those with some solid long term payers (3%).

I am trying to put together a portfolio right now and just starting to research it more in depth but I think I should be able to put together a decent protfolio to return around 6-7% in Divs + capitol gains over the long haul.

Other suggestion would be of the labor intensive variety. Yad work, reselling on Ebay/ Craigs etc.

Although if your a good salesman, you can start a yard service - you get the jobs, handle the contracts, then sub the work out. - take your cut and just have to follow up and make sure work is done.

Websites, and contracting out the things I do at my job. Over the past four years of doing this I've made roughly $15k total, and received about $3k in free/reduced medical care. It doesn't sound like a lot, but my free time spent on these projects is extremely low, 0-40 hours on average.